US3100767A - Water-soluble disazo dyestuffs - Google Patents
Water-soluble disazo dyestuffs Download PDFInfo
- Publication number
- US3100767A US3100767A US832167A US83216759A US3100767A US 3100767 A US3100767 A US 3100767A US 832167 A US832167 A US 832167A US 83216759 A US83216759 A US 83216759A US 3100767 A US3100767 A US 3100767A
- Authority
- US
- United States
- Prior art keywords
- acid
- parts
- sulfonic acid
- water
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 3
- 239000002253 acid Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- -1 for example Chemical class 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- IRPXADUBAQAOKL-UHFFFAOYSA-N chembl1408927 Chemical compound C1=CC=C2C(N=NC3=C4C=CC(=CC4=CC(=C3O)S(O)(=O)=O)S(O)(=O)=O)=CC=C(S(O)(=O)=O)C2=C1 IRPXADUBAQAOKL-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- MWKMQUZZZYRXBN-UHFFFAOYSA-N 2-aminochrysene-1-sulfonic acid Chemical class NC1=C(C=2C=CC3=C4C=CC=CC4=CC=C3C2C=C1)S(=O)(=O)O MWKMQUZZZYRXBN-UHFFFAOYSA-N 0.000 description 1
- BWQHQLOGZIBRON-UHFFFAOYSA-N 3-(aminodiazenyl)naphthalene-1,2-disulfonic acid Chemical compound NN=NC1=C(C(=C2C=CC=CC2=C1)S(=O)(=O)O)S(=O)(=O)O BWQHQLOGZIBRON-UHFFFAOYSA-N 0.000 description 1
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 1
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
Definitions
- This invention provides valuable new azo-dyestulfs which contain at least two strongly acid groups imparting solubility in water and which correspond to the formula 11-10 n-i tm HOaS in which R represents the radical of adiazo-component free from azo-linkages, land advantageously the radical of a benzene or naphthalene sulfonic acid, n represents the Whole number 1 or 2, X represents the radical of a halogenated 1:3:5-triazine of the formula Halogen bound through an amino-bridge, and especially Ian -NH bridge, in which formula Z represents the radical of a dyestufi bound through an NH bridge.
- the invention provides more especially monoazo-dyestuffs of the above formula, which contain a 2-chloro-4-amh1o- 1:3 :S-triazine radical of the formula
- the invention also provides a process for the manufacture of the aforesaid dyestuffs, wherein a trihalogen-l 3:5 triazine, especially 2:4:6-trichloro'1:3 :S-triazine, is con Bidfiflfi? Patented Aug. 13, 1963 in which R and n have the meanings given for Formula 1, and m is the whole number 1, 2 or 3, and, on the other with an amine of dyestuif character in such manner that a halogenated triazine condensation product is obtained.
- the starting dyestuffs of the Formula 2 there are used as coupling components, for example, 2- methoxy-1-aminonaphthalene-6-sulfonic acid and more especially l-aminonap-hth alene-6- or -7-sulf0nic acid.
- the diam-components to be coupled with the above coupling components may contain substituents that do or do not inrpart solubility in water, for example, strongly acid substituents imparting solubility in water, such as sulfonic acid groups.
- These diam-components may be either relatively simple compounds, for example, aminobenzenes', and sulfonic acids thereof, aminonaphthalene sulfonic acid, aminopyreneor aminochrysene-sulfonic acids or aminonaphthol sulfonic acids, or they may be more complicated diam-compounds free from azo linkages.
- the diam-compounds obtained, for example, by means of a mineral acid, especially hydrochloric acid, and sodium nitrite, may be coupled with the aforesaid aminonaphthalene sulfonic acids by "methods in themselves known.
- the condensation of the resulting amino-monoazodyestuffs with cyanuric chloride is carried out in such manner that the condensation product obtained contains two exchangeable halogen atoms, of which one is exchanged in the process of the invention for the radical of an amino-compound of dyestuti character.
- amino-compounds there may be mentioned above all aminomonoazo-dyestufis of the formula in which one Y represents a hydrogen atom and the other Y a sulfonic acid grouppand R represents a benzene radical which contains as the sole salt-forming substituent at sulfonic acid group in ortho-position to the azo linkage.
- the dyestuffs of this invention can be isolated and worked up into useful dry dyestuif preparations.
- the dyestuffs are advantageously isolated at a low temperature by salting out and filtration.
- the filtered dyestuiis may be dried, if desired, after the addition of an extender or buffer such as a mixture of equal parts of monosodium phosphate and disodium phosphate. The drying is advantageously carried out at not too high a temperature and under reduced pressure.
- the new 'dyestufis are suitable for dyeing and printing a very Wide variety ofrnaterials such as wool, silk, leather and superpolyamides, but especially cellulosic fibrous materials, such as linen, regenerated cellulose and above all cotton. They are'especially suitable for dyeing by the so-called pad dyeing process, in which the goods are impregnated with an aqueous dyestuff solution which may contain a salt, and the dyestuff is fixed by treatment with an alkali, advantageously at a raised temperature.
- This process and the direct dyeing process which can be used with many of the dyestuifs of this invention, yield valuable dyeings that are fixed fast to washing, and fast prints are obtained by printing. 7
- the dyeings and prints produced on cellulosic fibers with the dyestuffs of this invention are usually distinguished by their good fastness to light and above all by 17. 3 parts of 1-aminobenzene-4-sulfonic acid are stirred with 50 parts of ice, and an aqueous solution of 6.9 parts of sodium nitrile in parts by volume of water is added.
- the mixture containing the dyestufi" formed is adjusted to a pH-value of 7, and 18.6 parts of cyanuric chloride in a fine state of subdivision are added at 0 C. to the reaction mixture.
- the condensation is advantageously carried out at a pH-Value within the range of 8-6 and at a temperature Within the range of 510 C.
- the condensation product formed is precipitated by the addition of sodium chloride and filtered off.
- Example 2 22.3 parts of 1-aminonaphthalene-tS-sulfonic acid are stirred with 300 parts of cold water and parts of ice, 25 parts of hydrochloric acid of 30% strength are added, and diazotization is carried out With 7.1 parts of sodium nitrite. When the diazotization is finished, a solution of 22.3 parts of 1-aminonaphthalene-6-sulfonic acid in 200 parts of water, the solution being adjusted to a pH value of 7, is run in at a temperature of 5-10" C. In a few minutes coupling is complete.
- the dyestuff can be precipitated with sodium chloride.
- the amino-azo-naphthalene disulfonic acid so formed is condensed in the manner described in Example 1 with cyanuric chloride and the primary condensation product is isolated.
- This condensation product is suspended in 600 parts of Water, and a neutralized solution of 31.9 parts of 1-arnino-8-hydroxynaphthalene-3:6-disulfonic acid in 200 parts of water is added.
- the temperature is adjusted to 40 C. and the pH-value is maintained at 5.5-6 by the slow addition of a dilute solution of an alkali hydroxide.
- 30 parts of sodium carbonate are added, and the product is coupled at 0-5 C.
- thalene-fi snlfonic acid lene-3 :G-disulionic acid.
- 2 aminonaphthalene 4 8 di 1 aminonaphthalene 7 sul 2 mcthylamino 5 hydroxy 1 ominobenzene 3 sulfonic Yellow orange.
- sulionic acid iOnic acid. naphtha1ene-7-sulfonic acid. acid.
- n is a positive whole number of at 2 parts of the dyestuif of the formula SOaH- HO SOQH i C-NH are dissolved in 100 parts of water.
- a cotton fabric is padded at 60-80 C. with the resulting solution, and the excess of liquid is removed by squeezing untilthe fabric retains 75 of its weight of dyestuff solution.
- the impregnated fabric is dried, then impregnated at room temperature in a solution containing, per liter, 10 parts of sodium hydroxide and 300 parts of sodium chloride, the fabric is then squeezed to a weight increase of 75%, and it is then steamed for 60 seconds at 100-101 C.
- the fabric is then rinsed, treated with sodium bicarbonate solution of 0.5% strength, rinsed, soaped for hour at the boil in a solution of 0.3% strength of a nonionic detergent, and then rinsed and dried. There is obtained a scarlet red dyeing that is fast to washing and light.
- R is ortho-sulfophenyl
- one of the Xs and one of the Ys each represents a sulfonic acid group, the other X and the other Y being a hydrogen atom.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6277258A CH377019A (de) | 1958-08-11 | 1958-08-11 | Verfahren zur Herstellung neuer Azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3100767A true US3100767A (en) | 1963-08-13 |
Family
ID=4524513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US832167A Expired - Lifetime US3100767A (en) | 1958-08-11 | 1959-08-07 | Water-soluble disazo dyestuffs |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3100767A (de) |
| CH (1) | CH377019A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988802A (en) * | 1989-03-13 | 1991-01-29 | Basf Aktiengesellschaft | Reactive dyes with three reactive groups |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1351385A (en) * | 1971-03-01 | 1974-04-24 | Ici Ltd | Fibre-reactive azo dyestuffs containing halotriazine substituents |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1667312A (en) * | 1923-01-09 | 1928-04-24 | Society Of Chemical Industry In Basle | Azodyestuffs and process of making same |
| US2892829A (en) * | 1954-11-29 | 1959-06-30 | Ici Ltd | New monoazo dyestuffs |
-
1958
- 1958-08-11 CH CH6277258A patent/CH377019A/de unknown
-
1959
- 1959-08-07 US US832167A patent/US3100767A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1667312A (en) * | 1923-01-09 | 1928-04-24 | Society Of Chemical Industry In Basle | Azodyestuffs and process of making same |
| US2892829A (en) * | 1954-11-29 | 1959-06-30 | Ici Ltd | New monoazo dyestuffs |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988802A (en) * | 1989-03-13 | 1991-01-29 | Basf Aktiengesellschaft | Reactive dyes with three reactive groups |
Also Published As
| Publication number | Publication date |
|---|---|
| CH377019A (de) | 1964-04-30 |
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